Abietic and dehydroabietic acid are interesting diterpenes with a highly diverse repertoire of associated bioactivities. They have, among others, shown antibacterial and antifungal activity, potentially valuable in the struggle against the increasing antimicrobial resistance and imminent antibiotic shortage. In this paper, we describe the synthesis of a set of 9 abietic and dehydroabietic acid derivatives containing amino acid side chains and their in vitro antimicrobial profiling against a panel of human pathogenic microbial strains. Furthermore, their in vitro cytotoxicity against mammalian cells was evaluated. The experimental results showed that the most promising compound was 10 [methyl N-(abiet-8,11,13-trien-18-yl)-d-serinate], with an MIC of 60μg/mL against Staphylococcus aureus ATCC 25923, and 8μg/mL against methicillin-resistant S. aureus, Staphylococcus epidermidis and Streptococcus mitis. The IC value for compound 10 against Balb/c 3T3 cells was 45μg/mL.
Oxygenated aromatic abietanes are an important class of naturally occurring compounds in plants where they play specific ecological roles. However, limited availability from their natural sources hampers their exploitation for the development of new drugs to treat human diseases. Herein the benzylic oxidation of aromatic abietanes mediated by sodium chlorite and aqueous tert‐butyl hydroperoxide is reported. The method is regioselective for 12‐substituted derivatives and gives the 7‐oxo products, in good yields. Moreover, it conveniently replaces the use of toxic chromium reagents for this transformation. Preparation of 7‐oxo, 7‐oxo‐15‐hydroperoxy and 7‐oxo‐15‐hydroxy derivatives of other aromatic abietanes is also possible with this method. Furthermore, the reaction products were used as key intermediates for a short and facile semisynthesis of the naturally occurring picealactones A, B and C to disclose their anti‐proliferative activity for the first time.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.